Recently, I was talking to an intern here at Close.io. Someone who’s incredibly talented, very smart, hardworking and disciplined.

After a few weeks at Close.io he said, “Steli, I think things are going well, but I’m not sure I’m growing fast enough.”

First of all, if you’re not sure that you’re growing fast enough—you’re not growing fast enough.

In response to his statement I asked, “When was the last time you made a mistake at Close.io?”

He thought about it, but nothing came to mind.

Well, there’s your problem, I said.

Leave comfortable behind

The number one reason for him not growing was that he was being too cautious. He was too concerned about being perfect and doing everything right.

Taking all the right steps and not overstepping his boundaries or making any mistakes that might make us disappointed in him.

When he wasn’t sure about something, he wouldn’t ask any questions. He would wait.

In any other company he’d be well on his way to the top. He was still growing and learning, but not as fast as I thought he could. Not at the height of his abilities and talent.

So I asked him, “Why are you not pushing yourself more to get out of your comfort zone and make mistakes?”

He thought about it and replied, “I don’t want to look stupid.”

He admitted that he was sitting on a ton of questions, he just wasn’t asking them.

The more questions you ask, the more context you’ll get and the more you’ll understand. If you don’t ask questions when you’re new at a startup, that makes me concerned.

Yes, he admitted he had a lot more questions that he wasn’t asking. But he was also smart enough to realize that those questions would seem obvious to us. That his ideas and suggestions on how to make the business better and grow faster would be things we had already discussed years before. And for very sound reasons, we had not moved forward with those.

And that’s why he didn’t ask his questions. He didn’t want to get the response, “Aw, how cute. The intern is asking us why we don’t do x, y and z.”

He didn’t want to get the feeling of being junior, being inexperienced—being stupid.

Instead, he kept his mouth shut.

So I told him: The fastest way to smart is through stupid. There’s no way to get to smart really fast unless you’re comfortable with looking stupid in the name of progress.

Permission to be stupid

Yes, asking certain questions will make you seem inexperienced. Why? Because you are. And that’s okay.

But how will you get that knowledge and become experienced if you don’t ask any questions? You won’t.

I’m gonna tell you how you’re gonna get there: Slowly and painfully, by repeating mistakes and learning the lessons.

If you want to get to smart fast, act stupid.

You need to be in an environment where it’s safe to do so. You need to be in the type of company, working in the type of team with the type of people who will give you permission to make the mistakes you need to make in order to grow.

You shouldn’t work somewhere where that’s not allowed.

This doesn’t apply to just interns. It goes for everyone. Whether you’re an executive, C-level or a founder doesn’t matter.

We should all be learning, growing and making progress.

5 questions to ensure you’re making progress

Here’s a list of five fundamental questions you should ask yourself every single day.

When was the last time I made a big mistake?

What did I learn from that mistake?

When was the last time I felt stupid?

When was the last time I acted stupid?

When was the last time I asked a question and really learned something from somebody else?

If you ask yourself these questions and lack answers, that’s your answer to “Am I growing fast enough?”

Start getting answers to these questions and act accordingly. Get comfortable with the uncomfortable by stepping outside your comfort zone and start making mistakes.

Take risks.

Fail.

Get rejected.

Sound stupid.

Because if you do that and pay attention to why things happened the way they did, you will learn. And you will learn fast.

I’m curious to hear your thoughts on these tactics and I’d love to know when was the last time you made a mistake and learned from the experience.

Share your stupidity in the comments and let us all learn from it so we can take our hustle to the next level.